Holiday houses in Castle Rock

Driftless Cabin

Escape to this cozy cabin nestled among the trees on a classic driftless hillside. Our newly-renovated cabin comfortably accommodates up to four guests. Warm your feet by the real wood stove and roast marshmallows next to the fire pit (wood included!), hike the 200 foot elevation gain on the property, and watch the sunrise through the valley from our new, 4-person hot tub. You'll truly understand the Danish concept of "hygge" after a few nights snuggled up under the stars in this secluded cabin.

Tree Bear Cabin, on a 67 acre Tree Farm

Step away from the demands of life into this hidden gem. Tree Bear Cabin is a 100% real wood log cabin above the bustle of town, nestled among a 67-acre tree farm. Enjoy the quiet of the forest, and the cozy cabin interior. Play games on the wide lawn, explore the trails throughout the property, and make the most of your trip with our noon check-in time and 4 pm check-out times! Activities close by include fishing, kayaking, hiking, wine tasting, UTV Tours, and visiting local shops & Orchards!

Driftless Region Cabin/ Stream and Sauna

Settle into a quaint farmhouse nestled in a valley in the rolling, forested hills of the Driftless Region. Start your day with a cup of local coffee on the front porch. Go on a long walk or bike ride, then return to the cottage to cook, play board games, listen the record collection or visit Viroqua (25 minutes) for a farm-to-table 5-star dinner, or check out local music. Build a warm fire outdoors/ warm up by the gas stove indoors, or go down to the stream for a sauna by the cool water creek.

Larsen Rustic Secluded Log Cabin W/Outdoor Hot Tub

Secluded cabin hike the trails to the cave and ponds. Close to trout fishing stream or Mississippi for fishing. Bring you UTV and ride the private trails $30 per driver and 10 per passenger or rent an UTV 300.00 per day Approx 15 miles from Priarie Du Chein, close to canoe outposts for the Kickapoo, Wisconsin river. Has a gas ,charcoal grill,fire pit, pool table, fooseball, ping pong table. Smart TV Private UTV trails are closed Oct 15th thru mid Jan for hunting. Access to public UTV trails.

Eagle View Lodge - 1850's Log Cabin w/ Hot Tub

In the heart of the Driftless, atop the Mississippi , enjoy the tranquility of a centuries-old Appalachian cabin. Relax on the deck & take in dramatic sunsets, soaring eagles & glistening stars. Soak in the hot tub & gaze at the majestic Mississippi. Host unforgettable dinners in the screened deck & share stories by the fireplace. Only 30 mins from Viroqua & Prairie du Chien, experience the natural beauty of the driftless region - hiking, fishing, hunting, biking - whatever inspires you.

Cool quiet country cabin on boulders and 120 acres

Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

Riverside Chalet, LLC.

Welcome to the Wisconsin River! Our 1750 sq. ft. cozy riverside chalet features 300 feet of river frontage, master bedroom in the loft, deck overlooking the river, bunk beds, full kitchen, propane fireplace, firepit, and a natural spring running through the yard. The property offers stunning views from every room in the house as well as easy access to the river. Our location has a beautiful view, stunning in fact, but we are very close to Hwy. 60 and there is heavy traffic noise.

Unwind at Driftless Pines Cabin

Kick back and relax in this calm, stylish, and recently renovated space. Driftless Pines was completely updated (including a brand new hot tub) with one thing in mind, to create an amazing cabin experience with all the proper luxuries & amenities our guests could want or need. Spend a day on the breathtaking Wisconsin River (just down the road), visit a local favorite in Vickie's Cafe or partake in a wine tasting session at the gorgeous & scenic nearby Wild Hills Winery.

Hilltop Hideaway, Cabin in the Driftless Area

*New* Wi-Fi Available - Comfortable Amish built cabin located in the Driftless Area of Southwest Wisconsin, close to area towns but still in a private setting. We are close to many area attractions including the Wisconsin River, House on the Rock, Frank Lloyd Wright's Taliesin, The American Players Theater, Wisconsin Dells, and much more! The cabin is an ideal place to relax for both couples or families who would like to escape the city and spend some time in nature.

River Road Retreat

Relax with the whole family at this peaceful place to stay. Located one block from the Wisc. River, with a park across the street. Within walking distance of convenience stores, local winery 3 miles away. Within 1/2 Hr. of the House on the Rock, and APT. Walking trails and swimming pool within walking distance. Walking trails and swimming pool within walking distance. Besides the loft and main floor we have a kid friendly game room in the basement.

Paradise Point sleeps 2 Hot Tub

1 bedroom 1 bath with loft. Cozy home where you can see Paradise. This memorable place is anything but ordinary. Views for miles of the Mississippi River, bluff tops and you can soar with the Eagles. What a place to relax in the newly added hot tub while you enjoy the view in what is call "God's Country". This is promised to be a one of a kind view. The Deck with comfortable outdoor seating Located in the heart of WIsconsin's Driftless Region.